Rushmore

At Rushmore Academy, a millionaire mentors a 15-year-old boy, who pays little attention to his school work. He's not much interested in girls, either, and joins every club the school has to offer.
Eventually, he does fall for one of his teachers. To complicate matters, the millionaire is also in love with her. Cast as the tycoon is Bill Murray, and Olivia Williams plays the teacher who is desired by all.